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Type: Artigo de periódico
Title: The Stereochemistry Of The Addition Of Titanium Enolates Of N- Propionyl-oxazolidin-2-ones To 5- And 6-membered N-acyliminium Ions
Author: Pilli R.A.
Alves C.D.F.
Bockelmann M.A.
Mascarenhas Y.P.
Nery J.G.
Vencato I.
Abstract: The stereochemistry of the addition of the N-propionyl titanium enolates 2a and 2b to 5- and 6-membered 2-ethoxyearbamates 1a-f was investigated. The addition proceeded stereoselectively to afford the corresponding (2S,1'S)-2- substituted pyrrolidines as the major diastereoisomer. Despite the lack of reactivity between 2-ethoxypiperidine 1b and N-propionyl titanium enolates 2a and 2b, less bulky carbamate groups on 2-ethoxypiperidines 1d and 1f restored reactivity and the corresponding 2-substituted piperidines were obtained in moderate to good yields although with poor diastereoseleetion.
Editor: Elsevier Ltd
Rights: fechado
Identifier DOI: 10.1016/S0040-4039(99)00398-6
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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